Step 3: Start with the big rocks and big transportation legs
What are the key things you want to do on the trip that are non-negotiable? What cities or countries do you want to visit? Is there something key that you want to do that is only available on a specific day of the week?
I know I want to see whales and wildlife in Patagonia. I know I want to go to Uruguay, Paraguay and Iguazu falls. I want to see Buenos Aires but it can be all at once or as an in-between jumping off place in between other stops. I’ve looked at Cordoba and Salta but frankly they are second tier and it will depend on timing, transportation and costs.
Figure out the highlights of your trip and build an outline. Based on geography, for me it makes sense to do Patagonia and Iguazu falls in conjunction with each other since I will be flying.
For South America, the distances are so long that flying or long distance buses are the two most obvious options for transportation. But there is not one solution – every trip and location is different. In Central America I mostly used shuttles. In Jordan I hired a driver. In Eastern Europe I used the train while in the Balkans I always rented a car.
When I went to Central America, I was traveling from Nicaragua to Panama. The big rocks included Monteverde in Costa Rica and Panama City. It wasn’t until I found a rafting trip down the Pacuare river that would take me from Central Costa Rica to Caribbean Coast that stops in Peurto Viejo Costa Rica and Bocas Panama fell into place. If not for that (fabulous) rafting option for transportation, I may have traveled down the Pacific coast.
Step 4: Hotels, transfers and tours
We started big and are now starting to narrow down onto the details. Depending on your flexibility and time, this is where you can start to let go a little. While I would love to be more flexible and carefree, I hate spending precious travel time wondering around looking for a hotel.
This is a balance. Do your research but also know there is no perfect one answer. There are thousands of options and hundreds of them will fit your needs. Have an idea what you are looking for in order to narrow down your search (you can always throw it out the window later if you find an amazing option that you can resist). Do you just want somewhere clean to drop at night? Do you want to meet other travelers? Do you plan to spend some time at the hotel relaxing and want particular services and amenities? Do you want to be in the city center or outside the main tourist area? Consider the balance of cost and convenience with distance.
Trip Advisor is a great place to start. Trip Advisor will give you some wonderful options and first hand reviews. However, while their reviews are usually reliable, if you run across lodging on another sight that is not reviewed on Trip Advisor, it isn’t bad, it is just not reviewed!
Other good sights include booking.com, hotels.com, hotwire.com, other blogs, lonely planet, and hostelworld. Check out the cities tourism page. If you are in a larger group or staying for more than one night, check out Airbnb.
As you build your plan, think through your trip logically. Even if you intend to book it later or once you arrive, still think through your options and make some notes. Land at the airport – do you need a visa in advance? Get from airport to hotel? Oops, did you need to stop at an ATM to get money or did you get some before you left home? Dinner that night, I’ll just ask the hotel. Do any of the activities you want to do need a tour or reservations? How popular are they? Can you inquire in country or do you need to book beforehand?